Protective headgear, such as helmets, are often used in activities, such as bicycling, skateboarding, motorcycling, rock climbing, snowboarding, and skiing, that are associated with an increased risk of head injury. Typically, such protective headgear is designed to maintain its structural integrity and stay secured to the head of a wearer, while protecting the wearer from a trauma to the head. This is often facilitated by a retention system that secures the headgear to the head of the wearer, and a fit system that tailors the fit of the helmet to the size and shape of the wearer's head. Each of these systems often have several different points of adjustment. These multiple points of adjustment, however, may make it difficult for an inexperienced wearer to properly adjust and wear the headgear.